Catalytic Strategy for Conversion of Triacetic Acid Lactone to Potassium Sorbate

Abstract

This study shows a new route to produce potassium sorbate (KS) from triacetic acid lactone (TAL), which is a chemical platform that can be biologically synthesized from natural sources. Sorbic acid and its potassium salt (KS) are widely used as preservatives in foods and pharmaceuticals. Three steps are used to produce KS from TAL: 1) hydrogenation of TAL into 4-hydroxy-6-methyltetrahydro-2-pyrone (HMP), 2) dehydration of HMP to parasorbic acid (PSA), and 3) ring-opening and hydrolysis of PSA to KS. TAL can be fully hydrogenated over Ni/SiO 2 to give near quantitative yields of HMP. A three-step reaction kinetics model was developed for dehydration of HMP into PSA. This model was used to show that the highest PSA yield occurs at low temperatures. An experimental PSA yield of 84.2% with respect to TAL was obtained which agreed with the prediction of the reaction kinetics model. KOH was used as a coreactant for the ring-opening hydrolysis of PSA to produce >99.9% yield of KS from PSA. Tetrahydrofuran (THF) was used to purify the TAL derived-KS (TAL-KS). The TAL-KS had a KS purity of 95.5%. The overall yield of TAL-KS with respect to TAL was calculated to be 77.3%. TAL-KS produced in this study had similar antimicrobial activities as commercial KS.

Sustainable Triacetic Acid Lactone Production from Sugarcane by Fermentation and Crystallization

“…[14][15][16] Alternatively, sorbic acid can be produced from TAL through a series of reactions (namely hydrogenation, dehydration, ring-opening, and hydrolysis) with high overall yields (e.g., approximately 77% as potassium sorbate). 2,6 TAL does not currently have an established global market as the chemical synthesis route is prohibitively expensive. 5 However, the prospects for the biological production of TAL continue to improve, with recent advancements in the conversion of sugars and acetate by metabolically engineered strains of microbes including Saccharomyces cerevisiae, [17][18][19][20][21] Yarrowia lipolytica, 7,[22][23][24][25] Escherichia coli, 10,20,26 and Rhodotorula toruloides 27 (formerly classified as https://doi.org/10.26434/chemrxiv-2024-4sz8x-v2 ORCID: https://orcid.org/0000-0002-2620-2829 Content not peer-reviewed by ChemRxiv.…”

“…In the case of catalytic conversion of TAL to sorbic acid, intermediates (serially: 5,6dihydro-4-hydroxy-6-methyl-2H-pyran-2-one; 4-hydroxy-6-methyltetrahydro-2-pyrone; and parasorbic acid) can occur in a series of reactors (e.g., for hydrogenation, dehydration and ring-opening, and hydrolysis, respectively). 2,6 In the case of catalytic conversion of TAL to polydiketoenamine plastics, aliphatic dicarboxylic acids can be used along with TAL (stoichiometric coefficient n will depend on the structure of the targeted resin) to make bio-based monomers, which can be milled with amine monomers (1:1 stoichiometry with TAL) to make polydiketoenamine resins (chemical structures are not depicted for clarity, and theoretical maximum yields will depend on the aliphatic dicarboxylic acids used). 10…”

“…most probable values and ranges (detailed description on the choice of distribution type and range is included in Section S1 6. of the ESI).…”

Sustainable Triacetic Acid Lactone Production from Sugarcane by Fermentation and Crystallization

“…[14][15][16] Alternatively, sorbic acid can be produced from TAL through a series of reactions (namely hydrogenation, dehydration, ring-opening, and hydrolysis) with high overall yields (e.g., approximately 77% as potassium sorbate). 2,6 TAL does not currently have an established global market as the chemical synthesis route is prohibitively expensive. 5 However, the prospects for the biological production of TAL continue to improve, with recent advancements in the conversion of sugars and acetate by metabolically engineered strains of microbes including Saccharomyces cerevisiae, [17][18][19][20][21] Yarrowia lipolytica, 7,[22][23][24][25] Escherichia coli, 10,20,26 and Rhodotorula toruloides 27 (formerly classified as https://doi.org/10.26434/chemrxiv-2024-4sz8x ORCID: https://orcid.org/0000-0002-2620-2829 Content not peer-reviewed by ChemRxiv.…”

“…In the case of catalytic conversion of TAL to sorbic acid, intermediates (serially: 5,6dihydro-4-hydroxy-6-methyl-2H-pyran-2-one; 4-hydroxy-6-methyltetrahydro-2-pyrone; and parasorbic acid) can occur in a series of reactors (e.g., for hydrogenation, dehydration and ring-opening, and hydrolysis, respectively). 2,6 In the case of catalytic conversion of TAL to polydiketoenamine plastics, aliphatic dicarboxylic acids can be used along with TAL (stoichiometric coefficient n will depend on the structure of the targeted resin) to make bio-based monomers, which can be milled with amine monomers (1:1 stoichiometry with TAL) to make polydiketoenamine resins (chemical structures are not depicted for clarity, and theoretical maximum yields will depend on the aliphatic dicarboxylic acids used). 10…”